Lifestyle Review: Seattle, Washington

Or how I learned to love the wind and the trees

Charles Douglas-Osborn
6 min readNov 17, 2023
That isn’t the London Eye, but in the background that is Rainier Mountain!

When most people think about Seattle, they probably think about Starbucks. But there is much more to the city than Coffee (though I will say… there are a ton of coffee places there… maybe due to how north it is, which means the winters are darker?!). It is a beautiful, tree-ridden, hilly, water-based city, that was a delight to visit!

As always, if you’d prefer to see this in a shorter video form, here is my Vlog on Seattle:

This was a quicker one than usual with a little less editing — sorry!

Still working on how these vlogs fit into all the other things I want to do, but let me know how I can improve this format…

Affordability (2/10)

Photo by micheile henderson on Unsplash

Having lived in New York, I always imagined everywhere else being cheaper (probably a lot cheaper!), so it is always humbling coming to a new city and finding it is… pretty similar prices 😔

For Seattle, I think the reasons why people have flocked here are likely:

  • It’s a beautiful place to live
  • It’s close to Vancouver, so it's the default place for a lot of Canadians to move
  • Big Tech is ingrained here (it's basically Microsoft & Amazon HQ)
  • During the Pandemic, people wanted smaller cities & a certain drug being legalized here, helped give people even more reason to try it out.

I was finding that food out and about was actually more expensive than the default New York one too. You’ll see a ton of sports cars driving around, from the high-paid Tech people (or those that have now left after selling their stocks). In short, I’d say it is actually more than Denver and the closest I have found to New York since I started my travels.

Friends & Family (3/10)

Photo by Felix Rostig on Unsplash

Outside of LA, Seattle is basically the furthest you can be in the US from the UK. This, on top of yet another hour's time difference, means that it’s even harder to stay in contact with friends & family.

On this trip, I was able to connect with some friends, but most of them are planning on leaving the city. One of them was able to make a ton of friends in less than a year (early 20s), and the other was actively complaining about making friends (early 40s) after 5 years. There is something known as the Seattle Freeze (a similar term used in Vancouver), which is people are nice but have no intention of making friends.

I didn’t end up doing any activities that would make me friends, but on my walking tour, I was invited to drinks with some folks. Overall, it seems a bit risky as to whether I would find my “Niche” or “Clique”.

Dating (5/10)

Photo by Priscilla Du Preez 🇨🇦 on Unsplash

After a small mountain town, anything seems better for dating! The apps had way more people on them, you see way more people on dates and as someone not drinking at the moment, the coffee culture would make a ton of sense.

Alas, the only person I did end up meeting was from Vancouver and also trialing out the city like me. However, I was able to get lots of recommendations for where to live and what to do while I am in Vancouver so that was a plus 😀.

Culture (8/10)

You should have Satsquatched what happened next…

Very similar to Denver, there are several great venues & museums in the city. Again, I prefer having fewer venues which means that although there is less to do, you’d actually do it more (less is more).

It also has the MoPOP (Museum of Pop Culture), which is now my favorite museum of all time. As a big film & TV buff, the amount of content they have is amazing, from niche areas (like the models from Laika movies — the “Missing Link” pictured above) or mainstream content (like Luke Skywalker's lightsaber & fake hand from the Empire Strikes Back, pictured below):

When someone said to lend a hand, I think they misunderstood

Nightlife / Logistics (7/10)

View from West Seattle (The needle pictured on the left)

I was living next to Capital Hill, where there were a ton of cool-looking bars & restaurants. The city also felt very inclusive, with a lot of LGBTQ+ content everywhere and meeting many folks that I feel were able to be themselves in the city without the risk of judgment.

Over in Fremont and Ballard, there are tons of breweries as well. Some of which had non-alcoholic beers, something I never thought I would do (similar to Coke Zero… they taste like watered-down versions of the real thing, but as you drink more you get used to the added aqua).

Health & Fitness (8/10)

A view from a park, that is only 30 seconds from a main road

I was impressed by the number of beautiful parks within walking distance. The city itself is covered in trees, so there is a real feeling of being more connected with nature than I have felt in any other major city.

It is also very hilly, so you’ll get a proper workout for your calves and thighs for sure! Though I didn’t go too far out of the city (which would require a car), you can also do some real hiking well, with Olympic, Rainer & Mt. Baker-Snoqualmie, surrounding the city.

Although I never went in, I did find a ton of gyms as I walked around as well, so staying fit seems very doable here.

Job & Startup Opportunities (8/10)

Photo by Priscilla Du Preez 🇨🇦 on Unsplash

As mentioned above, Seattle is really the home of Amazon and Microsoft (just over the road in Bellevue). Being from the tech world myself, this would give me good opportunities for careers, or a large pool of people that I could sway to join my startup too.

I wasn’t able to engage with any startup stuff while I was there, but from everything I have read, there is a lot of potential!

The feel of the town (7/10)

View from the Gasworks (Where the “paintball fight” in “10 Things I hate about you” was filmed)

Overall, Seattle is a really cool city. It has pretty much everything you would want from a city. The main downsides are the weather during winter (which is basically London weather so I’m OK with that) and the distance away from the UK.

As such for now, I feel that if a great job opportunity came up that was based in Seattle, I would seriously consider it. As many folks know, I’ve always liked the idea of working at Microsoft, and so now I am good with applying to roles based in Bellevue in a way I was not before.

Having said that, I won’t actively be choosing Seattle I don’t think for now. However, it does now make it onto the board of places I would consider living which is exciting.

Also as I enjoyed seeing my friends and experiencing a city (rather than a town before), Digital Nomad has now increased a bit from where it was too. So here are the latest scores:

As always, thanks for reading!

I’m now starting to think about what I am going to do next year, at the moment at the top of the list are places like Australia, New Zealand, Indonesia, and Japan. But I would love to hear your recommendations in the comments (or feel free to message me!)

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Charles Douglas-Osborn

Previous Head of Product at NewtonX, Founder of Haystack and Merlin Guides, ex-Google, Entrepreneur, Pun-dit.